Potassium Carbonate → 5-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester

HRID 571746ノート

反応式

HRID 571746 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])(=O)=O>CC(C)=O.CN(C=O)C.C(OCC)(=O)C.[NH4+].[Cl-]>[F:29][C:25]([F:30])([CH:26]([F:28])[F:27])[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 37924752,2,3,3-Tetrafluoropropyl trifluoromethanesulfonateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

生成物 1

HCID 574758745-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester収率 66.4%

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

Methyl 5-hydroxypyridine-2-carboxylate (0.903 g, 5.90 mmol) is suspended in acetone (7 mL) and DMF (7 mL). 325 Mesh potassium carbonate (2.44 g, 17.69 mmol) is added in one portion and stirred at room temperature for 1.5 hours under nitrogen. 2,2,3,3-Tetrafluoropropyl trifluoromethanesulfonate (2.02 g, 7.67 mmol) is added drop wise and the mixture is stirred for 2 hours. The reaction mixture is diluted with ethyl acetate and saturated NH4Cl and extracted with ethyl acetate (3 times). The combined organic extracts are washed with brine, dried over Na2SO4, filtered, and the solvent removed in vacuo. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0-20% ethyl acetate in dichloromethane to give the title compound (1.047 g, 66%). ES/MS (m/e): 268.0 (M+1).

後処理

  1. stirringthe mixture is stirred for 2 hours
  2. extractionextracted with ethyl acetate (3 times)
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe crude product is purified by silica gel flash chromatography
  8. washeluting with a gradient of 0-20% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-e7b7d3f57c994e77bffbdf69ab6bebb9
出典データセット
uspto-grants-2015_05
特許番号
US09029367B2

反応ノート

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